I wish both parties would post "bounties" for tools they need that they don't have time to build. Much of it is built in the air for a highly specific context or bought off the shelf these days but there are some ongoing unsolved engineering needs.
Off the top of my head: I don't think there's a good solution to verify ad-buys in small markets. You could make a pretty penny sticking a webcam in front of an over-the-air broadcast TV in every county in every swing state and hiring someone to tick a box every time a candidate's ad plays.
Their Trello Board needs an election night camp for kids/childcare service. Older kids get a fun, educational camp where they can hold a mock election and learn about voting and democracy while you go vote. As a dad, if I promise my son something I'm 1000X more likely to actually do it. As a former volunteer I've lost track of the number of doors I've knocked where parents can't go vote because they need child care.
I helped with some of the UI for the boiler room in 2008. This article only touches on the GOTV and targeting aspects although the most exciting component would have been the ability to allocate human resources to contest improbable results in real time.
http://www.desmoinesregister.com/story/news/elections/presid...